Water → 1H-Indazole-5-carbonitrile
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.O.[CH3:54][N:55](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([C:54]#[N:55])=[CH:10][CH:9]=2)[CH:5]=[N:6]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 150 °C
Procedure
To a suspension of 5-bromo-indazole (2.0 g, 10.2 mmol), Zn(CN)2 (1.4 g, 12.2 mmol), and Xantphos (0.9 g, 1.5 mmol), in DMF (10 mL) and water (0.1 mL) was added Pd2(dba)3 (417 mg, 0.51 mmol) under N2 at rt. The suspension was heated at 150° C. for 1.5 h in the microwave. The solution was filtered and concentrated, and the residue was purified by silica gel chromatography (10-20% MeOH/DCM) to give 350 mg (24%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.62 (2H, s), 8.20 (2H, d, J=8.0 Hz), 10.56 (1H, br s).
Workup
- filtrationThe solution was filtered
- concentrationconcentrated
- customthe residue was purified by silica gel chromatography (10-20% MeOH/DCM)
Sources & evidence
- ORD record
- ord-477c461a16cd468e84fb914ab2728c60
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969343B2
Reaction notes
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